Dimethylamine → cyclopenta-1,3-diene;(1R)-1-cyclopenta-2,4-dien-1-yl-N,N-dimethylethanamine;iron(2+)

HRID 962992Notes

Reaction equation

HRID 962992 reaction equation
C(O[C@@H:5]([C-:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)[CH3:6])(=O)C.[CH-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:17].[CH3:18][NH:19][CH3:20]>CO>[CH3:18][N:19]([CH3:20])[C@@H:5]([C-:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)[CH3:6].[CH-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:17]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 15328554(r)-1-Ferrocenylethyl acetate

Product 1

HCID 15823231cyclopenta-1,3-diene;(1R)-1-cyclopenta-2,4-dien-1-yl-N,N-dimethylethanamine;iron(2+)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 10 l flask, 812 g of crude (R)-1-acetoxy-ethylferrocene from Example 2 was admixed under argon at 25° C. while stirring with 1.0 l of 50% strength aqueous dimethylamine solution and 1.0 l of methanol, with the temperature rising to 40° C. The reaction mixture was subsequently allowed to stand for 2 days at 25° C. The mixture was then evaporated at 50° C. in a waterpump vacuum to 1.1 kg and the residue was added to 2.0 l of 20% strength sodium hydroxide solution.

Workup

  1. customrising to 40° C
  2. customThe mixture was then evaporated at 50° C. in a waterpump vacuum to 1.1 kg
  3. additionthe residue was added to 2.0 l of 20% strength sodium hydroxide solution

Sources & evidence

ORD record
ord-9a89dd303d5f42138595678197e5b659
Source dataset
uspto-grants-1998_06
Patent number
US05760264

Reaction notes

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